Unexpected Second Chances
by MissCreativeInsanity
Summary: After her parent's death, Jessie figured that God had given up on her. But after a fight with her grandmother, a certain Archangel decides to prove her wrong. Thrown head first into a world she only thought of as fiction, she quickly learns it's not all fun and games. Monsters, demon and danger await her around every corner as she searches for her destiny, and a place to belong.
1. Chapter 1

_**Disclaimer:  
**_ _ **Hello. So before we begin, I'd like to say a few things. The first being I do not own Supernatural, any of the plot or the characters. I only own my OC and anything that goes along with her, or changes because of her. And it is a sister!fic (sorta), because being an older sibling I wanted to have a chance to write something from a younger sibling view point.  
**_ _ **Second, if she seems a bit Mary Sue please tell me. I didn't think she was, but you readers might find that different.  
**_ _ **Third, there are swears and derogatory terms in this fan fiction so if you can't handle those sort of things, please leave.  
**_ _ **That is pretty much all I can think of. Other than that, please enjoy, rate and review. I'm always happy to hear opinions!**_

* * *

"She's just an ugly, slutty, bitch!" Normally, Jessie was used to her grandmother's rants. Sixteen years of hearing them, generally prepares you for things like that.

Beatrice had a rather strong opinion, especially when it came to the teen's mother, Katelyn. She never liked her. She was always talking about how she was seeing her husband's friend behind his back, or spending too much money on the useless cars she had liked to fix up. Most of the time, Jessie just let her run herself out of steam. After all, after her parent's died , Beatrice had become her legal guardian.

And usually, her grandmother managed to keep it to herself. It would only come out if she drank too much.

Unfortunately, the woman was a bit of a drunk. So occasions like this happened a lot more frequently then Jessie would care to admit.

That night, was particularly bad. Instead of running out of steam this time, though, she just kept going and going. But now, she started to compare Katelyn to her daughter.

"You're just like her, you know?" She slurred, taking another swig of her beer. "Obsessing over all those cars in the back." Sitting across from her, the brunette clenched her fists, trying to stay calm. This was getting just a little too far for her to be comfortable. "Hell, one of these days you're gonna walk in here, pregnant from one of those pieces of trash you call friends."

Now, you need to understand this girl had been dealing with rants like this for the past five or six years, two of those even before her parent's died. So, by this point she was sick of hearing the trash talk.

"Stop it." She growled under her breath.

"Excuse me?" Beatrice questioned, glaring at her granddaughter. With her pale, dishevelled hair and wild eyed look she got once she's been drinking, she seemed to look even more crazy than usual. But, for once, Jessie was not backing down. Enough was enough. "What did you say?"

"Stop trashing my mother." She said louder. "That's all you ever say, day in and day out. And I'm sick and tired of it."

"Well, I'm sorry for telling the truth." That only made the sixteen year old angrier.

"No! That is your opinion." Standing up, she glared down at the old woman. "And it is completely wrong. My mother was the most honest, caring person I have ever met. Easily worth ten of you." The last part she spat before grabbing her sweater and walking to the door.

"Where do you think you're going?" Her grandmother shouted after her.

"Any where but here!" She shouted back, slamming the door behind her.

Shoving her hands into her pockets, she walked out towards the tree line just behind the house. During the day, it was one of her favourite places to be. Calming, with just the right amount of mystery. But right now, it was the only place she could think to go.

So even though it was way darker than she normally liked it to be when she went out, she pressed on. Far behind her, she could still hear Beatrice yelling at her to come back. Kicking leaves up as she went, she didn't stop till she got to a clearing about five hundred meters from the house.

During the day, it was lit bright by the sun. Its rays casting calm shadows over the ground. To tell the truth, it was a really beautiful place. But at night, it was a completely different matter.

The moon gave the entire area an eery glow. The shadows cast by trees resembled that of bony fingers, reaching out to ensnare anyone who dare walk close enough. Like some creepy scene out of her favourite TV show.

Letting out a shaky sigh, Jessie ran her fingers through her hair. Looking up at the sky, she frowned.

 _Why?_ She thought to herself. _Why the hell did you need to leave me here?_

"You couldn't have just let me be in the car with them, could you?" She questioned aloud, now glaring at the sky. "Or hey, maybe have sent me somewhere I might _actually_ be able to do something that matters." She added.

For a moment, she just stood there, staring at the sky. Part of her hoping that some one, some _thing,_ would happen that could act as some sort of answer. But that only ever happens on TV. Despite the lack of an answer, the teenager still wasn't ready to leave. Sitting down on the grass, she decided she much rather stay there, than go back and deal with her grandmother.

Unfortunately, before she knew it, she was falling asleep. Though, as she did, she failed to notice the figure appearing seemingly out of now where behind her.

"Some where you actually matter?" The man chuckled, crouching down to look at the teenager. For a few years now, he had been watching her, looking out for any trouble that may have gotten near her. More or less waiting for the moment she'd finally call on him, whether she realized it or not.

"Yeah, I think I can do that for you." Brushing her hair out of her face, he placed his index and pointer finger on her forehead. "I just hope you're ready." He muttered, just as there was a bright, white light and the sound of fluttering wings. And then the pair of them were gone.

Groaning, Jessie rolled over and pulled her blanket closer around herself. Some where off beside her, an alarm was going off.

"No..." The low moan left her mouth as she reached around, trying to shut off the alarm. While it worked at first, soon it was back up again.

"Come on sweet heart," A voice chuckled. "Up and at'em." At first, the sixteen year old didn't pay the voice much mind, thinking it was just her grandmother. That is, till she realized the voice was male.

Immediately, she was sitting up right, staring wide eyed in front of her.

"Good morning, Jessica." Staring back across from her was a man. His brown hair slicked back ever so slightly, a confident smirk on his lips. A smirk she had only seen on one other person. And last time she checked, he was a fictional character.

As those thoughts fired rapidly through her mind, his smirk grew.

"Don't worry, you're not going crazy."

"You sure," She counter, throwing the cover off of her legs. Dressed in comfy pyjamas that she didn't even dare think about how he them got on her. "Cause this feels pretty damn crazy to me." Though she gave a light laugh at the end of her sentence, she was anything but amused. "You," She pointed at him. "Are not real. You can't be real."

"Believe me," Laughing, the man stood up and walked towards her. It wasn't till he was crouching down to look her in the eyes, did he continue. "I am very real." As if to prove his point, he poked her forehead. "And just happen to be your, guardian angel."

Now it was her turn to laugh.

"Oh you have got to be kidding me." The cynical tone in her laughter was also reflected on her face. "I actually have a guardian angel. And he's the archangel Gabriel?" Said man only smirked. This just made her roll her eyes. "Alright, where is the freaking camera?" Pushing off the bed and past him, she began to look around the room for the hidden cameras.

"What?" He looked at her with a combination of confusion and insult.

"You can't be Gabriel." Jessie restated, turning to look at him. "Because one; he's from a freaking TV show and two; he died in season five. At best, you're Richard Speight Jr., and my friends got the bright idea to sign me up for some reality show." When all she got for a response was an unimpressed look, she continued to look for the cameras. Doing so for another five minutes before turning around to see the brown haired man only a foot from her.

"You really don't believe me?"

"Nope." She shook her head, crossing her arms over her chest. He just raised an eyebrow before snapping his fingers.

Immediately, everything around them changed. Rather than standing in what she had assumed was a crappy motel room, they were in the middle of a rain forest. In a torrential down pour. The air was thick with humidity, thunder and lightening. As a bolt crashed across the sky, the teenager stared up at the man, who smirked and snapped his fingers again.

Once again, they were in the motel room. Soaking wet.

"Still think I'm not real?" Gabriel questioned. She simply shook her head, unable to say anything.

"Okay," Jessie started, looking up from her coffee. After drying off and putting on a pair of clothes the archangel whipped up for her, they had gone to get some food from a local dinner. From what she could see, she was in Fairfax, Indiana. No where near her grandmother's house in Vancouver. "Let me get this straight. You're my guardian angel?"

"Yes." He nodded, taking a bite of his syrup soaked pancakes.

"And you've been watching over me since I was born?"

"Yup."

"And we're in a universe where the TV show Supernatural is real? In 2008?"

"Right on both accounts." He nodded, smirking at the disbelieving look on the girl's face.

"One more." She sighed, before giving him the most serious face she could muster. "Why?" There it was, the million dollar one. Swallowing what was in his mouth, Gabriel waited a moment before explaining.

"Because you asked me to." He said simply, enjoying the confused look on her face.

"When the hell did I say that I wanted to be here?" She questioned, freaking out ever so slightly. "I'm pretty sure I would have remembered saying something like that!"

He just shrugged.

"Those may have not been your _exact_ words, but I took them as I would." The smirk on his lips only grew larger as he continued. "You wanted to be somewhere that you could do something that _actually_ mattered. And here you are." As if to make a point, he spread his arms and gestured around him.

Jessie just sat there, staring at him disbelieving. How the hell did he think this was what she meant?

"So I can freaking die during the Apocalypse?" She nearly shrieked, quieting down when they got some concerned looks from the other patrons. "Nope. No thanks. I'll take my life, over a Lucifer and Micheal showdown any day."

"A drunk grandmother who only insults your dead mother?" He questioned, a frown on his face. "Going to school day in and day out, only to grow up and find some meaningless job?" The way he said it, made her life seem pretty dull actually. "Jessica Madeline York, you are capable of so much more."

"Like what?" She asked. "Hunting?" When he shrugged and gave a nod, she rolled her eyes and scoffed. "Gabe, I'm a freaking sixteen year old nerd. Do you know how bad that idea is?"

"Actually, not a bad one." He objected, their food long forgotten by this time. "If I remember correctly, you know nearly all there is to do with Hunting."

"Yeah, but that's just theoretical stuff." She countered. "Sure, maybe the research I could do, but the actual hunts, shooting a shot gun or killing something? No way." Shaking her head, she gave him a serious look. "I'm more likely to get myself killed."

"Not if some one trained you."

"Like who?" He simply smirked at the green-eyed girl, as if to say 'You already know who'. Of course, she did know who he had in mind. And she also thought it was a ridiculously stupid idea. "No."

"Oh come on!" He whined.

"No freaking way!" She objected, glaring.

"But they'd be perfect!" Gabriel tried again.

"And they'd think I'm just some silly little girl who's going to end up getting herself killed." Jessie pointed out. "At best, I get dropped off on Bobby's doorstep."

"You'd get training." He reminded, a smug look on his face.

"Worst, they end up telling Castiel or Zachariah finds me and I'm either A; sent back to my world, and to my dead end life, as you've so kindly pointed out." She glared. "Or B; he smites me on the spot for being more liable than a freaking prophet." At her words, the archangel's smile disappeared. Clearly, he hadn't really thought of it like that.

Feeling like she won, she gave him a smug look, before digging into her french toasts. As she did though, her mind began to think of what he had said. Maybe running into the Winchesters and getting trained by them wouldn't be the worst. At least she'd be doing something that mattered, despite the fact no one would know.

And honestly, if they did drop her off at Bobby's, she would still be relatively safe. For the most part. And the old Hunter would train her, simply out of principal for the fact she should know how to protect herself.

"Alright," She finally sighed, getting Gabriel to look up a her. "Let's just be hypothetical for a moment here. Say I some how managed to get Sam and Dean to agree to train me," A smile spread across his features. "How the hell am I suppose to even find them?" She questioned. "I mean, they travel all over America. It's damn near impossible to know where they're going to be next."

"Damn near," He nodded, agreeing. "If you haven't been keeping an eye on them like I have." At the curious look on his charge's face, he grinned. "You forgot that, didn't you?"

"Shut up." She rolled her eyes. "Where are they going to be next?"

"Oh, you don't worry about that." He smirked, reaching into his pocket and pulling out a couple papers. "If I were you, I'd be more focused on picking my classes for the start of year."

Raising an eyebrow in confusion, Jessie stared at him for a little bit before turning back to the papers. When she saw what one of them read, she groaned.

"You have got to be kidding me."  
 _ **Truman High, Home of the Bombers**_ was written in bold letters across the top of an exchange student enrolment form.


	2. Chapter 2

"That is it." Jessie growled, slamming the door to her Pines Motel room. "I freaking quit." Throwing her bag on the small couch, she jumped on her bed and buried her head in the pillows. "Send me back."

Appearing beside her on the bed, Gabriel looked down at the teenager with a smirk.

"Giving up already?" He questioned. "It's only been what? Three months?"

"Yes." She sighed, turning her head to give him a glare. "And nothing. No Winchesters, no things that go bump in the night, no nothing." Rolling over, she sat up. "All I've gotten out of this whole experience thus far, is a bunch of lore books and tomes," She gestured to the pile on her beside table. "That you insist I read."

"I thought you liked the spell books." The archangel raised an eyebrow.

When he first had brought the books over, she dived into the tomes immediately. Despite the fact that they were all written in Latin, she did her best to translate them, -slowly teaching herself the language in the process- and learn some of the spells. She had even made her guardian angel go and find her the things needed for certain hex bags.

If some one didn't know better, they'd have figured she was a witch in training. Which, she probably was becoming. Though, from what she knew from the show, she could become a good witch, the doesn't sell their soul to a demon, and still be a Hunter. And if she was being honest with herself, the idea of being a witch didn't seem that bad to her.

"Yeah, I do." She admitted, running her fingers through her hair. "They're great, actually." That made the angel smile. "What's not so great is the fact that I'm referred to as the 'Satanic Worshipper' at school." That, however made him frown.

It was true though. One day she had brought a tome to school, taking the advantage of the computers to try and work out a couple of more complicated translations -after that day, though, she forced Gabriel to get her a laptop- when one of the cheerleaders caught sight of a couple pictures in the book. It was the basic pentagram or devils trap -Jessie couldn't remember- but she got the wrong idea.

Next thing the brunette knew, all the cheerleaders, jocks or 'popular' people were making fun of her. On almost a daily basic she was being asked all these stupid questions about summoning the devil or making sacrifices. She was just lucky none of the teachers had overheard said questions, other wise she was almost certain she'd have a one way ticket to either the police station, or looney bin.

"Are you okay?" The brown haired man questioned, giving her a serious look. There was a moment of silence, before she sighed and shook her head.

"Yeah, I'm fine." A smirk slowly formed on her lips. "Maybe one of these days some demon is gonna show up and I'll save their sorry butts with some kick ass exorcism."

At that, both the archangel and the teenager laughed, probably finding the comment way funnier than it actually was. When they were done, they just sat in silence for a moment. Catching their breath and enjoying each others presence.

That was another thing she had learned. In the three months she had been there, Jessie had gotten closer to Gabriel. And while she can honestly say that he still was ever bit the smug trickster he was portrayed as in the show, he also was very caring, something that honestly surprised her. He was always making sure she was alright. That she had everything she needed, or that she was safe. As time went on, she saw more and more of the angel who had stood up to his brother to protect humanity.

"Okay." He finally spoke, breaking the silence as he stood up. "Come on, lets go." Looking up at him confused, Jessie raised an eye brow.

"Where exactly?" He simply smirked.

"Oh, I think it's time we made sure you were properly protected."

Turns out, what Gabriel had meant was she was going to get her first tattoo. An anti-possession tattoo. And while she would admit it was pretty bad ass looking, the next day at school her shoulder was killing her, not to mention she had gotten barely any sleep the night before due to tossing and turning, trying to find the right position to sleep in that wouldn't hurt her shoulder. This had only made her mood sour, and and her attitude down right unfriendly and ill tempered towards a majority of her classmates.

"Oh, look who it is." Ashley, the tall blonde that basically lead the Bombers Cheerleaders, sneered as the brunette and April -probably her only friend that she had made in her three months at Truman- walked out of their English class. "Did your ruler contact you yet, Demonic Slut?"

 _Watch who you call that._ She thought to herself. _Because I'm almost positive you've banged close to triple the amount of guys I have. Which, by the way is zero._

"Aww." Another cheerleader laughed when they got no response. "Look, she's pretending to ignore us. Cute." Clenching her fist, she felt her bad mood worsening. Though trying to ignore it, she decided to just push past them.

Of course, though, like all bullies, they didn't let it go.

"Hey, Skank." Ashley called, her hands on her hips. "We weren't finished talking to you!" Turning, Jessie glared at them, taking note of how stupid they looked wearing their uniforms.

"Virg a butmon levithmong!" She recited, giving the group of girls a dark look.

"What did you just say?" The blonde shrieked, having guessed what the brunette had said wasn't exactly friendly.

"Oh nothing." She smirked. "Just told all my demon friends that you and the whole cheer squad are free game." And with the shocked and slightly fear filled looks on their faces, Jessie turned on her hill and walked towards the cafeteria, April in tow.

"Alright, is it just me," The large girl started, staring at her friend nervously. "Or are you just in a bad mood?"

"No." She sighed, getting in line for food. "I'm not having the best day." When she got no answer and saw the other girl giving her a look to continue, she chuckled and rolled her eyes. "Fine, quit hounding me. I was up all night, tossing and turning because of my shoulder."

"What happened?"

Rather than answer, she simply turned her back to her and slipped her arm out of the left side of her flannel -something she seemed to wear quite often- and pulled the fabric aside to reveal the skin. Sure enough, standing out against her pale skin was the black ink that made up the anti-possession tattoo.

"Oh my god!" April gushed, giving Jessie a wide eyed look when she turned around, a smile on her lips. "You seriously got a tattoo?"

"Yup." She nodded, grabbing a plate of spaghetti and one of salad. "My host dad took me out to get it last night."

"Okay, I seriously need to meet him." She joked, only causing them both to laugh. Soon, they were sitting at their usual table and dug into their meal. As far as school cafeteria food went, Truman had some pretty good food.

"So," April started. "Did you really put some curse on them?" With her head, she gestured to the cheerleaders sitting a table or two over. Following her gaze, the brunette simple rolled her eyes and chuckled.

"No."

"Well, what did you say?"

"It was a deprivation of Latin." She smirked. "It more or less means to breed with the mouth of a goat." At this, the other girl stared at her before they both erupted into more laughter.

Of course, Jessica had been lying. She had actually just used the fake Enochian exorcism from the episode seventeen from season five. Though, if she had told her friend that she knew there was no way she would believe her.

For the next couple of minutes, the two just chatted. Not about anything in particular. Just normal, teenage things. And for a moment, Jessie was almost able to forget where she was, and her life back in her world. For a moment, she felt normal.

That is, until she heard the conversation going on at the cheerleaders table.

"She totally banged Jamie Jaffe, that's what." Ashley's voice easily carried over the lunch room, drawing the attention of a few of the others students.

"Great." April sighed, not quite believing that the blonde had to bring down another student. While she seemed disgusted, Jessie stared at the group with a sort of sadness and annoyance, mixed with a hint of fear. She remembered exactly when this conversation was in the show. She also remembered the events that followed.

"She gave him the reverse cowgirl and everything." The smug look on the head cheer leader's face made her want to puke. Noticing this, her friend gave her a concerned look.

"Hey, you alright?" Turning her attention from the table, she sighed and nodded.

"More or less." She reassured her. When April gave her a look that clearly said she didn't believe her though, she rolled her eyes. "I'm just sick and tired of Ashley's behaviour, alright."

"Isn't everyone?" She countered, before adding. "Hey, maybe one of these days you could use some of that mumbo jumbo you're always reading about, and curse her." Though she knew the brunette was just joking, she couldn't help but consider the idea for a short moment. Of course, she then thought of what happened to all those witches who use their magic to harm others.

"No, she's not worth the effort." She chuckled in response. Just as she did, she heard the familiar chant from the cheerleader table.

"Slut, slut, slut, slut, slut, slut." The chant continued on, putting all eyes on the girl it was directed too. Fighting the tears burning at the back of her eyes, Taylor quickly walked away from the group she had called her friends, and over towards the only, relatively empty table.

For a moment, both Jessie and April watched as the girl sat down at the other end of their table. Neither spoke, till the brunette felt the need to finally say something.

"You shouldn't listen to those jerks." Though she knew the comment was well meant, the green-eyed sixteen year old gave her friend a look that clearly said 'Shut Up'. Part of her believed if she maybe changed the events of this single conversation, she could prevent April from getting arrested.

"Leave me alone." Was all Taylor said in response, giving the two a look. It was painfully evident to anyone that the cheerleaders' taunts were getting to her.

"I just mean-"

"April." Jessie hissed, trying to stop. Unfortunately, it didn't work.

"I'm sorry, that's all." And at that single moment, she knew it was done. April had sealed her fate, and there was nothing Jessica could do to change it. All she could do was watch as the distraught girl looked up at her friend with disgust.

"You?" She asked, on the edge of a sneer. "You're sorry?" Sensing things would not be going in a good direction, the larger girl tried to direct her attention back on her lunch but it was too late. "Don't you feel sorry for me, you fat, ugly pig."

Eyes wide, April looked at her with shock. Though, it quickly morphed into sadness. With tears stinging in her eyes, she quickly left the table, only to leave Jessie there, glaring.

"Well, look at you." She growled, giving Taylor the deadliest look she could as she pushed her chair back. "Just because they're being bitches and ass holes to you, does not mean you get to take it out on those only trying to help."

The rest of that day, Jessie couldn't find April. She had looked throughout the entire school, and nothing. So, the next day, she was considerably on edge when she arrived at the school. The beginning of the After School Special episode had kept playing through her mind, over and over again the night before.

"Come on." She mumbled to herself, running down the hallway. "Don't let me be too late." Despite already knowing the outcome of that morning, she was desperately hoping that maybe, just maybe, there was still a chance that she could stop Dirk. So, armed with a couple iron nail and a thing of salt, she made her way to the first floor bathroom.

Though, when she was halfway down the hall, she heard a scream at made her blood chill.

"Shit!" Running to the door, she tried to push it open the find that it was locked. "No, no, no!" Backing up a little, she tried ramming her shoulder into it, ignoring the stinging pain from the tattoo. Over and over again, she repeated the action, doing her best to block out the desperate cries she could hear from with in.

By this point, one of the teachers had heard the thuds of her body against the door and came out to investigate.

"Hey!" Mr. Murphy called, running up to her. "What's going on?"

"I heard a scream." Jessie grunted, trying yet again to force the door open. "And I can't get the door open!" Just as she said those words, though, the door gave way, causing her to fall onto her side.

"You're ugly." At hearing her friends voice, she looked up in time to see ectoplasm leaking from her eye like a tear. Lying at her feet, was Taylor's soaked and lifeless body.

* * *

 _ **Disclaimer: I do not own any of the original Supernatural characters or plot. I just own my OC.  
**_


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